The Courage to Fail - A veteran’s lesson for entrepreneurs

Sergeant Willy looked at me up and down, chomping on his chewed-up cigarette while sizing me up. “Lo”, he growled, “get your fuckin’ ass to Air Assault - or I’ll tear you a new one”. He didn’t mince words, continuing relentlessly. “Either man up or fuckin’ stay home”.

That was 10 years ago, shortly after I enlisted in the Army.I was an arrogant 23 year old, armed with feigned self belief, thinking that I was better than others.I was an Honor Graduate from Army Basic Training, graduating top of my class, and had graduated with Honors from the University of Chicago.But inside I was cowardly, and Sergeant Willy had just called me out.

The fact was that I was scared to join Air Assault school, one of the elite Army schools.I was scared about the unknown.But most importantly, I was scared to fail and look like a fool in front of my fellow soldiers.
Sergeant Willy knew that.He had led hundred, if not thousands, of soldiers before me, and looked through me in a way only a great leader could.He wanted me to forget about myself, to free me of my self-doubts, to embrace challenges fully. In short, he wanted to teach me to have the courage to fail.
Fast forward 10 years - now as an entrepreneur and Associate at TechStars NYC. And during my time here, I’ve admired one startup that has embraced the lesson that Sergeant Willy so wanted me to learn.
That startup is Sketchfab.Three French co-founders, who dropped their lives and wives to come to New York to pursue the American dream, fighting tooth and nail out of Paris so they could earn a shot in the US.Three strangers in a strange land, learning to fail themselves as they abandon their cultural shackles and adopt a new American way of business, mustering the courage to say goodbye to their past.Three friends that have bonded over all things 3D, embracing the future of “YouTube for 3D files”.
We in the tech industry embrace entrepreneurs that have tenacity andhustle as key personality traits. Part of the reason is that it demonstrates the ability to execute business development and partnership opportunities, which are the early indicators of a possible revenue model. The thinking, as it goes, is that if a founder can hustleearly customers, surely that behavior can be turned into a monetizable model.
But I posit that tenacity and hustle can be learned, and that the true personality trait that should be embraced is courage.Courage is what drives founders to leave their lives and embrace new ones like Sketchfab; courage is what enables founders to constantly change and adapt to new challenges; courage is what allows founders to quickly fail, and in turn, quickly succeed.
When I think back to the person that taught me about courage - deep down inside I have no idea if Sergeant Willy is still alive, or one of the thousands taken by the war.If he were alive, I don’t even know if he would remember me.
But I do know this. Sergeant Willy taught me about courage in a way no one else could.And I honor his legacy by demanding that same courage that he saw in me.